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Isomerism in Alkenes

Isomerism in Alkenes

Alkenes like 1-butene and 2-butene exhibit constitutional isomerism, as they differ in the position of the double bond. Further, 2-butene exhibits stereoisomerism and exists as two distinct compounds differing in spatial arrangement.
An isomer is called cis-2-butene when the methyl groups are on the same side of the double bond, and the other stereoisomer, in which methyl groups are on the opposite side of the double bond, is called trans-2-butene. The cis and trans stereoisomers are not...

Conformations of Cycloalkanes

Conformations of Cycloalkanes

Adolf von Baeyer attempted to explain the instabilities of small and large cycloalkane rings using the concept of angle strain — the strain caused by the deviation of bond angles from the ideal 109.5° tetrahedral value for sp3 hybridized carbons. However, while cyclopropane and cyclobutane are strained, as expected from their highly compressed bond angles, cyclopentane is more strained than predicted, and cyclohexane is virtually strain-free. Hence, Baeyer’s theory that...

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...

[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement

[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement

The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.

Halogenation of Alkenes

Halogenation of Alkenes

Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.

Disubstituted Cyclohexanes: cis-trans Isomerism

Disubstituted Cyclohexanes: cis-trans Isomerism

Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers....

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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

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Strain-Inducing Positional Alkene Isomerization.

Vignesh Palani¹, Alison E Wendlandt¹

¹Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.

Journal of the American Chemical Society

|August 30, 2023

Summary

Researchers developed a new method for creating strained cyclobutene molecules from cyclobutylidene precursors. This strain-inducing alkene isomerization uses photocatalysis and a co-catalyst, offering a mild route to valuable synthetic building blocks.

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Area of Science:

Organic Chemistry
Photocatalysis
Medicinal Chemistry

Background:

Small, strained ring systems are crucial in medicinal chemistry and organic synthesis.
The instability of strained organic molecules makes their preparation difficult.

Purpose of the Study:

To develop a mild and selective method for accessing cyclobutene building blocks.
To utilize a strain-inducing positional alkene isomerization reaction.

Main Methods:

Employing a decatungstate polyanion photocatalyst and a cobaloxime co-catalyst.
Utilizing readily obtained cyclobutylidene precursors.
Investigating mechanistic pathways through detailed studies.

Main Results:

Achieved mild and selective synthesis of cyclobutene building blocks.
Demonstrated the versatility of cyclobutene products via strain-releasing transformations.
Identified a steric basis for strain-selective product formation.

Conclusions:

The reported strain-inducing isomerization provides efficient access to valuable cyclobutene intermediates.
The synergistic photocatalyst and co-catalyst system enables energy storage via ring strain.
The methodology offers a versatile platform for organic synthesis and medicinal chemistry applications.